If you were watching the Super Bowl halftime show in 2025 and saw Serena Williams basically C-walking to Kendrick Lamar’s "Not Like Us," you probably had a moment of "Wait, what?" It wasn't just a random cameo. There is deep, messy lore there. Everyone wants to know when did serena and drake date and why things seem so incredibly awkward a decade later.
Honestly, the timeline isn't as clean-cut as a Wikipedia entry. It’s a "slow burn" that turned into a very public cold war.
The Early Days: 2011 to 2014
People first started whispering about these two way back in 2011. Drake was suddenly the biggest tennis fan in the world. He was spotted in the stands at Serena's matches, looking way more invested than your average spectator.
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At first, they played it off as a friendship. They’ve known each other for years, but the vibe was always... heavy. Drake even dropped that line in "Worst Behavior" back in 2013 about playing tennis at the crib and swearing he could beat Serena with her left hand. It was flirty. It was playful.
But according to some insiders, the timing was just off. Drake was supposedly the one constantly asking, "When are we going out?" while Serena wasn't entirely sure if he was serious or just being a rapper. They were definitely "something" during this period, but it wasn't the official, red-carpet-debut kind of romance yet.
That Infamous Italian Dinner in 2015
If you want the exact moment the world got confirmation on when did serena and drake date, it was August 2015.
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They were caught in Cincinnati. Not at a club or a massive event, but tucked away in a private room at an Italian restaurant called Sotto. Someone snapped photos of them getting very cozy—lots of hugging and what definitely looked like a kiss.
This was the peak. Drake was at almost every one of her matches that summer, including a high-stakes run at Wimbledon. Fans were calling him her "lucky charm," though that didn't last long. When she lost the U.S. Open later that year, some (unfairly) tried to blame the "Drake Curse."
By the end of 2015, the fire had mostly fizzled out.
The Lyrics and the Fallout
The weirdest part of this whole story isn't the dating; it's the aftermath. Drake doesn't usually let things go quietly. In 2016, he released "Too Good" with Rihanna. For years, people speculated who it was about.
Then, in 2024, a video surfaced from an old studio session. Drake flat-out told his mom the song was about Serena. The lyrics are pretty biting: "I'm too good to you / I'm way too good to you / You take my love for granted / I just don't understand it."
He basically felt rejected. He felt like he was putting in all this effort—flying overseas to see her—and she wasn't matching his energy. Shortly after they drifted apart, Serena met Reddit co-founder Alexis Ohanian. They got engaged in late 2016 and married in 2017.
Drake seemingly took that personally.
Why the drama still matters in 2026
You'd think after ten years and two kids, everyone would have moved on. Nope. In 2022, Drake dropped "Middle of the Ocean" and threw a random stray at Serena’s husband: "Sidebar, Serena, your husband a groupie / He claim we don't got a problem but / No, boo, it is like you coming for sushi."
Alexis Ohanian’s response was actually pretty legendary. He basically said, "Yeah, I'm the best groupie for my wife and daughter."
The tension boiled over during the Drake vs. Kendrick Lamar feud. Kendrick specifically rapped, "Better not speak on Serena," which was a direct reference to Drake's weirdly persistent comments about her marriage. When Serena showed up at the Super Bowl in 2025 to dance to the Drake diss track, she effectively picked her side.
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Summary of the Timeline
- 2011–2014: The "Friends with Tension" phase. Lots of match appearances and flirty lyrics.
- August 2015: The "Cincy Kiss." This is the peak dating period.
- Late 2015: The breakup. They "fizzled out" due to bad timing and misaligned expectations.
- 2016: "Too Good" is released (the breakup anthem).
- 2022–2025: The "Messy Ex" phase. Drake makes jabs in songs; Serena responds by supporting his rivals.
Basically, they dated seriously for a few months in 2015, but they've been arguing about it through song lyrics and public appearances for over a decade. It’s one of those rare cases where the breakup lasted much longer than the actual relationship.
If you're looking for more celebrity deep dives, check out the history of the "Drake Curse" or look into the full breakdown of the 2025 Super Bowl cameos.